Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B

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发布日期 2015-11-30

DOI 10.1039/C5QO00367A

影响因子 5.281

作者

Emma K. Davison, Jonathan Sperry

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摘要

In the presence of 1 mol% of a copper(II) catalyst and air, a readily available N1-acetyl-N3-thioacylguanidine undergoes a one-pot benzylic oxidation–oxidative heterocyclization sequence to give the 3-amino-5-acyl-1,2,4-thiadiazole core of polycarpathiamines A (2) and B (3) and thus facilitating the first synthesis of both natural products. This methodology offers a straightforward alternative to the low yielding dipolar cycloaddition used to access 3-amino-5-acyl-1,2,4-thiadiazoles.

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来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B

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